The Art of Speculation

Carret’s 1930 book, grown out of a series of articles he wrote for Barron’s, is one of the earliest systematic attempts to separate speculation from gambling. He treats speculation as the deliberate assumption of risk in the pursuit of profit and then works through the analytical apparatus for doing it well — reading a balance sheet, valuing a bond against an equity, judging management, sizing positions, thinking about the cycle. Carret had founded the Pioneer Fund in 1928 and ran money for another six decades, which gives the book the odd status of being both a period document of the late-1920s market and the working method of an investor who survived what came next.

Why it’s on the list: Pre-dates Graham and Dodd, and was written by a man who kept investing for sixty years after the crash the book was published into. The discipline described here is what the manias on the rest of this list lacked.

Where I saw it: @tylercosgrove’s October 15, 2025 list of 25 books he offered to send to Jared Kushner.

Connections

• Investing — the discipline the book sets out to define.
• Value Investing — Carret’s analytical method anticipates much of what Graham later codified.
• Benjamin Graham — the contemporary whose framework this book pre-dates.
• Risk — the book’s definition of speculation is built on the deliberate assumption of it.
• Market Cycles — the 1920s market Carret was writing inside of.